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Synthesis and QSAR study of novel cytotoxic spiro[3H-indole-3,2 '(1 ' H)-pyrrolo[3,4-c]pyrrole]-2,3 ',5 '(1H,2 ' aH,4 ' H)-triones
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2012 (English)In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 47, p. 312-322Article in journal (Refereed) Published
Abstract [en]

1,3-Dipolar cycloaddition reaction of 1-aryl-1H-pyrrole-2,5-diones 1a-e with non-stabilized azomethine ylides, generated in situ via decarboxylative condensation of isatins 2a-c and sarcosine (3) in refluxing ethanol, afforded 4'-aryl-5'a,6'-dihydro-1'-methyl-spiro[3H-indole-3,2'(1 ' H)-pyrrolo[3,4-c]pyrrole]-2,3',5'(1H,2'aH,4'H)-triones 4a-o in good yields. Compound 4I exhibited high anti-tumor activity against HEPG2 (liver cancer) cell line (IC50 = 12.16 mu M) compared to that of Doxorubicin (IC50= 7.36 mu M), and the other synthesized compounds revealed moderate anti-tumor properties against HCT116 (colon), MCF7 (breast) and HEPG2 (liver) human tumor cell lines. 3D-Pharmacophore modeling and quantitative structure-activity relationship (QSAR) analysis were combined to explore the structural requirements controlling the observed anti-tumor properties. It was found that the major structural factors affecting potency of these compounds were related to their basic skeleton.

Place, publisher, year, edition, pages
2012. Vol. 47, p. 312-322
Keyword [en]
1H-pyrrole-2, 5-diones, Azomethine ylides, Spiro[3H-indole-3, 2 '(1 ' H)-pyrrolo[3, 4-c]pyrrole], Anti-tumor, QSAR
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Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-86247DOI: 10.1016/j.ejmech.2011.10.058ISI: 000301169800034OAI: oai:DiVA.org:su-86247DiVA, id: diva2:586529
Available from: 2013-01-11 Created: 2013-01-11 Last updated: 2017-12-06Bibliographically approved

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